Organizations have emerged as more prominent players on the business scene as compared to individuals. The main advantage of an organization is its capacity to bring people with different skillsets and perspectives together to follow a specified course. However, the organizational setup creates many challenges that the group and its leaders have to overcome to sustain the business operations’ viability. The business landscape keeps shifting constantly, and one of the main trends in recent years has been the emergence of e-tailers. Roxie Steele is the founder and CEO of a fashion e-tailer known as StreetFashion.com, an e-tailer that majors in stylish and fashionable clothes for women. While the tale of her rise as an entrepreneur is remarkable, she is currently faced with a series of tough decisions on addressing different business facets. However, some past decisions depict a disturbing pattern of poor decision-making that paints Ms. Steele in lousy light.